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Contiguous concerted participation in the rearrangement of anti-tricyclo[4.2.1.1.2,5]deca-3,7,-diene-9,10-diol, a highly hindered system.

✍ Scribed by Christopher W. Doecke; Peter J. Garratt

Publisher
Elsevier Science
Year
1981
Tongue
French
Weight
181 KB
Volume
22
Category
Article
ISSN
0040-4039

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✦ Synopsis

The acid cataZysed rearrangement of to 2a is shown to proceed through concommitant eLectrophiZic and nucleophilic -attack on an alkene by an incipient carbonium ion and the remaining aZcoho2 function.

📜 SIMILAR VOLUMES

C,C-Double Bond Participation in the Aci
C,C-Double Bond Participation in the Acid-Catalyzed Cyclization of 9exo-Methyl-anti10,11-tricyclo[4.2.1.12,5]deca-3,7-diene-9endo, 10endo-diol. Influence of Steric Compression on the Product Distribution
✍ Gerardo M. Ramos Tombo; Sarmistha Chakrabarti; Camille Ganter 📂 Article 📅 1983 🏛 John Wiley and Sons 🌐 German ⚖ 408 KB 👁 2 views

## Abstract Acid treatment of 9__exo__‐methyl‐__anti__^10,11^‐tricyclo[4.2.1.1^2,5^]deca‐3,7‐diene‐9__endo__, 10__endo__‐diol (**8**) leads to the two isomeric pentacyclic ethers **7** and **9** by intramolecular nucleophilic substitution of a protonated OH‐group with participation of a C,C‐double

Nucleophilic Addition to C,C-Double Bond
Nucleophilic Addition to C,C-Double Bonds. Part VIII. The standard enthalpies of formation of anti9,10-10endo-hydroxytricyclo [4.2.1.12,5]deca-3,7-dien-9-one and 9-Oxatetracyclo [5.4.0.03,10.04,8]undec-5-en-2-one and kinetic data for the cyclization of the olefinic alcohol to the ether
✍ Alan A. Smeaton; William V. Steele; Gerardo M. Ramos Tombo; Camille Ganter 📂 Article 📅 1983 🏛 John Wiley and Sons 🌐 German ⚖ 258 KB 👁 2 views

## Abstract In view of the significance of steric compression in the base‐catalyzed intramolecular cyclization of polycyclic olefinic alcohols, the standard enthalpies of formation of __anti__^9,10^‐10 __endo__‐hydroxytricyclo [4.2.1.1^2,5^]deca‐3,7‐dien‐9‐one **(1)** and 9‐oxatetracyclo [5.4.0.0^3